(4-(4-(Methylsulfonyl)phenyl)piperazin-1-yl)(morpholino)methanone

ID: ALA3103355

PubChem CID: 76328252

Max Phase: Preclinical

Molecular Formula: C16H23N3O4S

Molecular Weight: 353.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1ccc(N2CCN(C(=O)N3CCOCC3)CC2)cc1

Standard InChI:  InChI=1S/C16H23N3O4S/c1-24(21,22)15-4-2-14(3-5-15)17-6-8-18(9-7-17)16(20)19-10-12-23-13-11-19/h2-5H,6-13H2,1H3

Standard InChI Key:  DBPAFWMBSKHHSG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   28.1016  -29.5279    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.6924  -30.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5096  -30.2360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8108  -28.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8096  -29.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5177  -29.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2273  -29.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2245  -28.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5159  -27.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9307  -27.8855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6372  -28.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3413  -27.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3424  -27.0684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6333  -26.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9231  -27.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0502  -26.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7579  -27.0684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0502  -25.8426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7545  -27.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4582  -28.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1683  -27.8877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1702  -27.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4621  -26.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3942  -29.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 17 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  5  1  1  0
  1 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3103355

   [4-(4-Methylsulfonylphenyl)piperazin-1-yl]-morpholin-4-ylmethanone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 353.44

Molecular Weight (Monoisotopic): 353.1409

AlogP: 0.66

#Rotatable Bonds: 2

Polar Surface Area: 70.16

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.78

CX LogP: -0.11

CX LogD: -0.11

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: -1.74

References

1. Flanagan JU, Atwell GJ, Heinrich DM, Brooke DG, Silva S, Rigoreau LJ, Trivier E, Turnbull AP, Raynham T, Jamieson SM, Denny WA..  (2014)  Morpholylureas are a new class of potent and selective inhibitors of the type 5 17-β-hydroxysteroid dehydrogenase (AKR1C3).,  22  (3): [PMID:24411201] [10.1016/j.bmc.2013.12.050]

2. Endo, Satoshi S and 16 more authors.  2017-10-26  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.  [PMID:28976752]

Source

Source(1):

• Scientific Literature